scholarly journals Experiments Towards the Synthesis of the Ergot Alkaloids and Related Structures. Part 8.17 The Total Synthesis of 4-Methyl-2,3,4,4a,5,6-hexahydro-benzo[f]quinoline-2-carbonitrile Hydrochloride Hemihydrate, an Immediate Precursor of the Despyrrole Analogues of Lysergic Acid and Its Amides

2002 ◽  
Vol 17 (3) ◽  
pp. 137-154
Author(s):  
Mark A.E. Bowman ◽  
Ralph E. Bowman ◽  
Roy V. Davies ◽  
Gerry Haran ◽  
Paul J. Harris ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Ergot Alkaloids ◽  
Lysergic Acid

scholarly journals Heterologous Expression of Lysergic Acid and Novel Ergot Alkaloids in Aspergillus fumigatus

2014 ◽  
Vol 80 (20) ◽  
pp. 6465-6472 ◽  
Author(s):  
Sarah L. Robinson ◽  
Daniel G. Panaccione
Keyword(s):  
Aspergillus Fumigatus ◽  
Candidate Genes ◽  
Mass Spectra ◽  
Ergot Alkaloids ◽  
Lysergic Acid ◽  
Precursor Feeding ◽  
Gene Encoding ◽  
Content Type ◽  
Multiple Reactions ◽  
Important Pathway

ABSTRACTDifferent lineages of fungi produce distinct classes of ergot alkaloids. Lysergic acid-derived ergot alkaloids produced by fungi in the Clavicipitaceae are particularly important in agriculture and medicine. The pathway to lysergic acid is partly elucidated, but the gene encoding the enzyme that oxidizes the intermediate agroclavine is unknown. We investigated two candidate agroclavine oxidase genes from the fungusEpichloë festucaevar.lolii×Epichloë typhinaisolate Lp1 (henceforth referred to asEpichloësp. Lp1), which produces lysergic acid-derived ergot alkaloids. Candidate geneseasHandcloAwere expressed in a mutant strain of the moldAspergillus fumigatus, which typically produces a subclass of ergot alkaloids not derived from agroclavine or lysergic acid. Candidate genes were coexpressed with theEpichloësp. Lp1 allele ofeasA, which encodes an enzyme that catalyzed the synthesis of agroclavine from anA. fumigatusintermediate; the agroclavine then served as the substrate for the candidate agroclavine oxidases. Strains expressingeasAandcloAfromEpichloësp. Lp1 produced lysergic acid from agroclavine, a process requiring a cumulative six-electron oxidation and a double-bond isomerization. Strains that accumulated excess agroclavine (as a result ofEpichloësp. Lp1easAexpression in the absence ofcloA) metabolized it into two novel ergot alkaloids for which provisional structures were proposed on the basis of mass spectra and precursor feeding studies. Our data indicate that CloA catalyzes multiple reactions to produce lysergic acid from agroclavine and that combining genes from different ergot alkaloid pathways provides an effective strategy to engineer important pathway molecules and novel ergot alkaloids.

Isolation of ergovaline, ergoptine, and ergonine, new alkaloids of the peptide type, from ergot sclerotia

1979 ◽  
Vol 57 (13) ◽  
pp. 1638-1641 ◽  
Author(s):  
Rudolf Brunner ◽  
Peter Leopold Stütz ◽  
Hans Tscherter ◽  
Paul Albert Stadler
Keyword(s):  
Total Synthesis ◽  
Ergot Alkaloid ◽  
Ergot Alkaloids ◽  
Extraction Processes

The isolation of three new ergot alkaloids of the peptide type from sclerotia of Clavicepspurpurea and from mother liquors of rye ergot alkaloid extraction processes is described. The constitution of the new alkaloids ergovaline, ergoptine, and ergonine has been established by comparison with compounds previously obtained by total synthesis.

scholarly journals Total Synthesis of (±)-Lysergic Acid, Lysergol, and Isolysergol by Palladium-Catalyzed Domino Cyclization of Amino Allenes Bearing a Bromoindolyl Group

2008 ◽  
Vol 10 (22) ◽  
pp. 5239-5242 ◽  
Author(s):  
Shinsuke Inuki ◽  
Shinya Oishi ◽  
Nobutaka Fujii ◽  
Hiroaki Ohno
Keyword(s):  
Total Synthesis ◽  
Lysergic Acid ◽  
Palladium Catalyzed

ChemInform Abstract: Photocyclization of Enamides. Part 29. Dehydrogenation with Benzeneseleninic Anhydride in the Total Synthesis of Ergot Alkaloids.

ChemInform ◽  
1990 ◽  
Vol 21 (27) ◽  
Author(s):  
I. NINOMIYA ◽  
C. HASHIMOTO ◽  
T. KIGUCHI ◽  
T. NAITO ◽  
D. H. R. BARTON ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Ergot Alkaloids

scholarly journals Correction to Total Synthesis of Lysergic Acid

2014 ◽  
Vol 16 (4) ◽  
pp. 1269-1269 ◽  
Author(s):  
Satoshi Umezaki ◽  
Satoshi Yokoshima ◽  
Tohru Fukuyama
Keyword(s):  
Total Synthesis ◽  
Lysergic Acid

scholarly journals Validation of a New Sensitive Method for the Detection and Quantification of R and S-Epimers of Ergot Alkaloids in Canadian Spring Wheat Utilizing Deuterated Lysergic Acid Diethylamide as an Internal Standard

Toxins ◽  
2021 ◽  
Vol 14 (1) ◽  
pp. 22
Author(s):  
Jensen Cherewyk ◽  
Taylor Grusie-Ogilvie ◽  
Barry Blakley ◽  
Ahmad Al-Dissi
Keyword(s):  
Spring Wheat ◽  
Matrix Effects ◽  
Limit Of Detection ◽  
Ergot Alkaloids ◽  
Internal Standard ◽  
Lysergic Acid ◽  
Lysergic Acid Diethylamide ◽  
Relative Standard ◽  
Validation Parameters ◽  
Sensitive Method

Ergot sclerotia effect cereal crops intended for consumption. Ergot alkaloids within ergot sclerotia are assessed to ensure contamination is below safety standards established for human and animal health. Ergot alkaloids exist in two configurations, the R and S-epimers. It is important to quantify both configurations. The objective of this study was to validate a new ultra-high performance liquid chromatography tandem mass spectrometry (UHPLC-MS/MS) method for quantification of six R and six S-epimers of ergot alkaloids in hard red spring wheat utilizing deuterated lysergic acid diethylamide (LSD-D3) as an internal standard. Validation parameters such as linearity, limit of detection (LOD), limit of quantification (LOQ), matrix effects, recovery and precision were investigated. For the 12 epimers analyzed, low LOD and LOQ values were observed, allowing for the sensitive detection of ergot epimers. Matrix effects ranged between 101–113% in a representative wheat matrix. Recovery was 68.3–119.1% with an inter-day precision of <24% relative standard deviation (RSD). The validation parameters conform with previous studies and exhibit differences between the R and S-epimers which has been rarely documented. This new sensitive method allows for the use of a new internal standard and can be incorporated and applied to research or diagnostic laboratories.

Dehydrogenation with Benzeneseleninic Anhydride in the Total Synthesis of Ergot Alkaloids

1996 ◽  
pp. 529-532
Author(s):  
Ichiya Ninomiya ◽  
Chiyomi Hashimoto ◽  
Toshiko Kiguchi ◽  
Takeaki Naito ◽  
Derek H. R. Barton ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Ergot Alkaloids

Physiological Effects of Schizophrenic Body Fluids

1959 ◽  
Vol 105 (438) ◽  
pp. 1-18 ◽  
Author(s):  
Edith G. McGeer ◽  
Patrick L. McGeer
Keyword(s):  
Ergot Alkaloids ◽  
Body Fluids ◽  
Lysergic Acid ◽  
Mental Illnesses ◽  
Lysergic Acid Diethylamide ◽  
Organic Basis ◽  
Physiological Effects ◽  
Chemical Agents ◽  
Mental Disturbances

Controversy has raged for over half a century as to whether schizophrenia, the most severe of all mental illnesses, could have an organic basis or whether its origin lay strictly in the psyche. Over the years, physiologists have probed into almost every aspect of the soma in the quest for some abnormality which would account for the schizophrenic syndrome. Many possibilities have been considered, investigated to a degree and then abandoned when definitive answers were not forthcoming. A dominant approach throughout has been the search for some psychotoxic material circulating in schizophrenic body fluids. Activity has been spurred by the recurrent recognition that chemical agents such as the ergot alkaloids, mescaline, bulbocapnine and lysergic acid diethylamide (LSD-25), could induce in normal persons transient mental disturbances similar to those seen in schizophrenia.

Sign in / Sign up

Export Citation Format

Share Document